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One of my closest friend come from "old money" family. They came from abroad and used to be very wealthy. How wealthy? With their own plane and pilot kind of wealthy. Due to political reason, the money was long gone. Both parents passed away now. No inheritance.
Anyway, he's in his early 40 now. With a huge McMansion, 1 part time maid, 2 fancy cars. Never anything worse than BMW. He owned a porsche too. Worked on similar management position as me(make about the same money). We sometimes talk about cars, financial stuff, our kids etc.. He don't cook, like to eat out, 2 big vacations every year with the whole family (Europe, Far East, cruise etc). Oh, he recently got a lease of a brand new BMW too. "Return the car when the lease is done, no need to worry about car breaking down.." He said. He told me he don't save a lot for retirement, $200-300k maybe.
He doesn't know my net worth and he always think I am poorer because the way I save and never seem to buy a newer car all these years. He rather enjoy it now than delaying until retirement 'cos "God knows if I'll still be around to spend it". I don't blame him. He witness the ups and downs from super rich to being average joe like me. He likes to talk to me a lot. Deep down, I think he want to see how average people save without his necessary luxuries. I feel like he asked because he wants to see if he can live that way too. Once I said I never have a maid, do my own laundry, no house cleaning lady, driving the same car for 14-15 years kind of scary him away.. He's a good friend and the only friend coming from true "old money" family. I am trying to dial him down a bit to more or less like us average joe, save a little more for the future. We'll see.
I don't think your friend really represents an American version of "old money", but more like a foreign-born version of "rednecks with money". I've known people who come from "old money", and they tend to live fairly modestly:
A nice family home in a very nice upscale suburban neighborhood but hardly a mansion or McMansion.
A "country home" or "beach cottage" or "camp" depending upon locale, generally located in some expensive locale like the Hudson Valley or Cape Cod or the Adirondaks, usually fairly large and rambling but not particularly imposing, and frequently this home has been in the family for generations and the ownership is shared among siblings or cousins.
Newer cars, more likely a Lexus or a Lincoln than a BMW.
They may have a cleaning lady/service and a lawn service. If they live in NYC, they may have a driver or use a car service. They have parties catered.
They send their kids to private schools but sometimes public schools depending upon where they live.
They're largely inconspicuous from most upper middle class people in regards to their spending and life-styles, which is likely why they still have so much of their "old money".
What you will frequently find in the homes of people with "old money" is expensive art and old furniture. Some of the furniture may be priceless antiques, others not so much, but it all has a history. People with old money pass the "good stuff" down to their children rather than have estate sales.
Well, that is what you do on a message board... you ask for and get comments. But the OP's recent posts have been about comparing himself to others, and that is not a good thing to do.
Sometime drop the comment about how much you have put away for retirement, and discuss some of the nightmares you have seen from folks who haven't put away enough.
I know a lot of old money families and none of them live like your friend. However, I've seen adult children of new money living like that with no understanding of the value of money. They basically are just waiting to collect their inheritance.
I suppose someone could grow up in a third world country where rich people have servants and never adjust to American economics.
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